N-alpha-(9-Fluorenylmethyloxycarbonyl)-N-beta-(2-trimethylsilyl)ethoxycarbonyl-L-2,3-diaminopropionic acid

Teoc, a silicon based amino-protecting group, which can be removed with fluorides as in TBAF. Highly orthogonal to Fmoc and Cbz chemistry; towards conditions of Boc chemistry the Teoc group is not sufficiently stable. Literature: The ß-(Trimethylsilyl)ethoxycarbonyl amino-protecting group; Tsao, J.-H.; Fell, E.; Hettrich, G.; Carpino, L.A.; Ringsdorf, H. J. Chem. Soc., Chem. Comm. 1978; 358-359. A New Silicon-Based, Fluoride Cleavable Oxycarbonyl Protecting Group Highly Orthogonal to the Boc-, Fmoc- and Cbz-Groups; Martin Golkowski and Thomas Ziegler; Molecules 2011; 16: 4695-4718. Begum Mothia, Antony N. Appleyard, Sjoerd Wadman, and Alethea B. Tabor; Synthesis of Peptides Containing Overlapping Lanthionine Bridges on the Solid Phase: An Analogue of Rings D and E of the Lantibiotic Nisin; Org. Lett. 2011; 13(16): 4216-4219. DOI: 10.1021/ol201548m. P. Sieber; Helv. Chim. Acta 1977; 60: 2711. H. Gerlach; Helv. Chim. Acta 1977; 60: 3039.